Process of manufacturing dialkyl barbituric acid.



, UNITED STATES PATE T orrron.

o'rro wo rEsor naairsrsnr, canals-Y. ASSIGXOR T LOUIS MERCK, EKBlANFI-IL .itct's'r unncK, ,wrLnEmr annex-imp CARL EBDIAXIIELM'ERCK, c PAn'rxEns as FIRM or E.

ga ancn, or-mnns'ranncnmrmr.

'3 PROCESS or mmac'ronma mamnnannmmc non Specification ot Letters' Patent.

Patented Dec; 22, 1908.

Original application filed September-22, 1905, Serial No. 279,689. Divided and this application filed April 6.19074 Serial No. 366,675.

T 0 all whom it may concern:

I} Be it'known that I, Orro WoLFEs, doctor of philosophy, a subject of the Emperor of Germany, residin at the city of Darmstadt,

in the Empire of certain new and useful Improvements in the Processes of Manufacturing Barbituric Acids, of which the following is a specification.

The present application is a divisional application from my application Serial No.

279,689, filed September 22, 1905, and covers Specifically the manufacture of barbituric acids, employini djalkyl malonylhaloids as starting mater! t I have ascertained that'if guanyl-urea is condensed=-with dialkyl malonylchlorid of the following general formula:

Alk'yl co.c1

condensation products are obtained which Germany, have invented are probably mixtures of several substances 3 for the reason that guanyl-urea is enabled react in two pseudomen'c forms: i w 00 an /m a) C\NH,. This unsymmetrical form can be condensed with the above-mentioned deri atives to substances of the two following typical formulas: -.1. xn,-co -c|:=o

' film n.\'-c=o 2. xn -om-c o formulas, when heatedwith aqueous acids,

are easily converted into dialkyl barbituric acid of the well-known formulaz nag-To 2 Al 00 T I palsy] Epcot The following equations illustrate the chemistry of the transformation of the prod-, ucts l, Q-and 3 into (halkyl barbitunc ac d,' by sapomfication: 6 1. NH;CO T-t|2=0 I Alkyl HN=C o:

J A1kyl,. -HN-c;.0 '70 H-T-C=0 A1kyl CC) \Alkyl f d- 15 2. -z-'n', o-x-,cl=o

i m x c c a H 9 Alkyl +3 KIN-0:0 I a H.I (l7=0 8o ,AIkyI 0 c 0,442

.=uk 1 HR =D in 'Ho N=fi 2 ,CQ I C v EN-0:0

H.TT=O

4 Allrvl o 2. co cum.Tl +0 rlm I mz-c=o The essential characteristics of the process thus indicated will be seen from what 15 common to the following specific example. Free guanyl-urea 'and dieflul mnlonyl 45 is under the Same circumstances d fi I cfiZorid.-l0 grams of guanyl-urea which was to substances mula The substances of these three typical of the following typical for- I prepared from, the hydrochlorid by shaking It with silver oxid'and evaporat' "the soluremoved by leaching in water. 7 The residue ether, and the'saltswere waq'HieSdiVH in cold diluted aniinoniat 51rd..

the ammonia, after the filtration 'oi-ithe liquid was boiled away or neutralized by vacetic acid. The derivative of pyrim'idin. crystallized-in fi'nezhard needles which decomposed-above 300 degrees-G. "The substariee is-soluble in alkali, ammonia, and in p fiying bmbansje; uric acid of 37%,-

- 1: fill Wing n w {described my invention and in wh'atmanner the sa'meis to' be performed,

batbiturie" arid; consisting in condensing "guanyleurea w ithd'iallgyl malonyl ehloriri of the following general formula:

whatlclaim and desire to? secure by Letters hygheating the mixture of the said'suhstauces diethyl bar itu'rie ad was 'readily'pbt-z in'ed.

The 1 process of mg iiftemri g' clielkjl and safio i fyi'ng the reult product by-"reaetingthis pro mineral acid.

' witnesses.

'e,H 700.91 0,11 com by heziting' the mixture of the said substances .and saponifying the'reslflting condensation product .by reacting this product with a 35 In testimony whereof I have hereunto set my hand in the presenee' f .two subscribing oT'ro WOLFES.

- .Witnes'sesi WALTER SCHUMANN, WALTER HAUSING. 

